In June 2014, forces of the “Islamic State” (a.k.a. ISIS, ISIL, or Da’esh) began probing the Jordanian border, leading to skirmished with Jordanian border forces and intense anxiety within Jordan. Until that point, Jordan had essentially lain low – maintaining as low a profile as possible even as violence erupted across most of its borders (including in Syria, Iraq, Israel, and Palestine). Yet Jordan was not a true neutral in the Syrian civil war either. Reports suggested that Jordan was connected to both arming and training of ‘moderate’ rebel forces against the Asad regime. Jordan then took the unprecedented step of engaging in air strikes on ISIS targets in Syria. When Da’esh staged a horrific execution of a captured Jordanian pilot, the regime declared that “the gloves had come off.” Jordan increased its air strikes on ISIS and refused to rule out ground troops in either Syria or Iraq. But as pressure built amongst its allies (the U.S., Saudi Arabia, GCC states in general) to increase its military role in Syria, Jordan seemed to grow more cautious regarding its level of intervention against either Asad or ISIS – and Jordan’s role in both conflicts remained deeply controversial within Jordanian domestic politics. These sometimes conflicting policies were complicated still further by the massive influx of Syrian refugees into Jordan, as the country attempted to deal with yet another challenge. Analysis and Conclusions This paper shows how Jordan’s multiple challenges and sometimes conflicting policies together amounted to an enormous and even dangerous gamble regarding ISIS, the outcome of the Syrian civil war, and its own domestic support and internal security. This paper examines Jordanian policy regarding each of these three key areas, as the Jordanian regime attempted to survive the threats of ISIS, the Syrian Civil War, and even the domestic challenges of the Arab Spring era. Regime focus on the former (external) threats, I argue, threatened to completely derail hopes on the domestic front for meaningful reform and change. Methods This paper draws on extensive field research, including with Jordanian government and opposition figures. Interviews include Islamist and leftist opposition activists, parliamentarians, government ministers, and several meetings with King Abdullah II. Panels? If accepted, this paper could fit with a diverse range of panels, including those on Jordan, the Syria civil war, ISIS, regional security, foreign policy-making, regional relations, or re-assesssments of the outcomes of the ‘Arab Spring’.